Fucoxanthin

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 178.197.236.32 (talk) at 11:19, 2 November 2013 (some useful links). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Fucoxanthin
Names
IUPAC name
Acetic acid [(1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethylcyclohexyl] ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.212.315 Edit this at Wikidata
  • InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1 ☒N
    Key: SJWWTRQNNRNTPU-XJUZQKKNSA-N ☒N
  • InChI=1/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1
    Key: SJWWTRQNNRNTPU-XJUZQKKNBP
  • CC(=CC=CC=C(C)C=CC=C(C)C(=O)CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=C=C3C(CC(CC3(C)O)OC(=O)C)(C)C
Properties
C42H58O6
Molar mass 658.920 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Fucoxanthin is a xanthophyll, with formula C42H58O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm.

Some metabolic and nutritional studies carried out on rats and mice at Hokkaido University indicate that fucoxanthin promotes fat burning within fat cells in white adipose tissue by increasing the expression of thermogenin.[1] A subsequent double-blind placebo-controlled human study of females with liver disease using supplementation with seaweed extract containing fucoxanthin in combination with pomegranate seed oil [2] showed in an average 4.9 kg (11 lb) weight loss in obese women over a 16-week period.[2]

Another 16-week trial is currently underway that is investigating the effects of a combination supplement of brown seaweed extract (containing fucoxanthin) and pomegranate seed oil. This study is looking at the effects of this supplement on body composition, resting energy expenditure, blood pressure, and serum lipid levels and liver enzyme levels of obese men and women following a hypocaloric diet. A manuscript involving the complete results of this study is still pending.

See also

References

  1. ^ Maeda, H; Hosokawa, M; Sashima, T; Funayama, K; Miyashita, K (2005). "Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tissues". Biochemical and Biophysical Research Communications. 332 (2): 392–7. doi:10.1016/j.bbrc.2005.05.002. PMID 15896707.
  2. ^ a b Abidov, M.; Ramazanov, Z.; Seifulla, R.; Grachev, S. (2010). "The effects of Xanthigen in the weight management of obese premenopausal women with non-alcoholic fatty liver disease and normal liver fat". Diabetes, Obesity and Metabolism. 12: 72. doi:10.1111/j.1463-1326.2009.01132.x.

Other studies

  • Haugan, J (1994). "Isolation and characterisation of four allenic (6'S)-isomers of fucoxanthin". Tetrahedron Letters. 35: 2245. doi:10.1016/S0040-4039(00)76810-9.